Processes for preparing calixarenes

Abstract

This invention relates to a process for preparing a calixarene compound by reacting a phenolic compound and an aldehyde in the presence of at least one nitrogen-containing base as a catalyst to form the calixarene compound. The invention also relates to processes for high-yield, high solid-content production of a calixarene compound, with high selectivity toward a high-purity calix[8]arene compound, without carrying out a recrystallization step.

We claim: 
     
       1. A process for preparing a calixarene compound, comprising:
 reacting a phenolic compound and an aldehyde in the presence of at least one nitrogen-containing base as a catalyst to form the calixarene compound, wherein the nitrogen-containing base is a tetraalkyl ammonium hydroxide, wherein each alkyl moiety in the tetraalkyl ammonium hydroxide is independently C 1  to C 2  alkyl. 
 
     
     
       2. The process of  claim 1 , wherein the tetraalkyl ammonium hydroxide is tetramethyl ammonium hydroxide. 
     
     
       3. The process of  claim 1 , wherein the tetraalkyl ammonium hydroxide is tetraethyl ammonium hydroxide. 
     
     
       4. The process of  claim 1 , wherein the phenolic compound is phenol, an alkyl phenol, or an arylalkyl phenol. 
     
     
       5. The process of  claim 4 , wherein the phenolic compound is a para-C 1 -C 24  alkyl phenol, benzyl phenol, or cumyl phenol. 
     
     
       6. The process of  claim 1 , wherein the aldehyde is formaldehyde or paraformaldehyde. 
     
     
       7. The process of  claim 1 , wherein the molar ratio of the phenolic compound to the aldehyde ranges from about 1:1.5 to about 1.5:1, and the molar ratio of the phenolic compound to the nitrogen-containing base ranges from about 200:1 to about 20:1. 
     
     
       8. The process of  claim 1 , wherein the reaction is carried out in the presence of an organic solvent. 
     
     
       9. The process of  claim 8 , wherein the mass ratio of the phenolic compound to the organic solvent is no less than 0.25:1. 
     
     
       10. The process of  claim 1 , wherein the reaction is carried out under reflux conditions. 
     
     
       11. The process of  claim 1 , wherein the aldehyde is paraformaldehyde and the reaction is carried out without reflux. 
     
     
       12. A one-step process for preparing a calixarene compound, comprising:
 reacting a phenolic compound and an aldehyde in the presence of at least one nitrogen-containing base as a catalyst to form the calixarene compound in a one-step process, wherein the nitrogen-containing base is a tetraalkyl ammonium hydroxide, wherein each alkyl moiety in the tetraalkyl ammonium hydroxide is independently C 1  to C 6  alkyl. 
 
     
     
       13. The process of  claim 12 , wherein the phenolic compound is phenol, an alkyl phenol, or an arylalkyl phenol. 
     
     
       14. The process of  claim 13 , wherein the phenolic compound is a para-C 1 -C 24  alkyl phenol, benzyl phenol, or cumyl phenol. 
     
     
       15. The process of  claim 12 , wherein the aldehyde is formaldehyde or paraformaldehyde. 
     
     
       16. The process of  claim 12 , wherein the molar ratio of the phenolic compound to the aldehyde ranges from about 1:1.5 to about 1.5:1, and the molar ratio of the phenolic compound to the nitrogen-containing base ranges from about 200:1 to about 20:1. 
     
     
       17. The process of  claim 12 , wherein the reaction is carried out in the presence of an organic solvent. 
     
     
       18. The process of  claim 17 , wherein the mass ratio of the phenolic compound to the organic solvent is no less than 0.25:1. 
     
     
       19. The process of  claim 12 , wherein the reaction is carried out under reflux conditions. 
     
     
       20. The process of  claim 12 , wherein the aldehyde is paraformaldehyde and the reaction is carried out without reflux.